Track 2 of 12 on Wings & Prayers and Second Flight

Tailwind (Up, Up, Up)

Flying is better with friends, so the whole gang catches the same wind together.

Soaring with friends

The friendship song. The Tailwind gang arrive by name: Cruising Captain, Wind Reader, Aviation Ace. And the invitation is instant: “Room for one more? Let’s fly!” A tailwind is the wind at your back, and the chorus refuses to fight it: you don’t paddle, you don’t push, you let the happy wind decide. Flying is simply easier with friends alongside, which is the whole point. Its EDM remix is track nine.

In the storybook, Chapter Three: Tailwind shares this song’s name.

Watch the music video.

Flight notes: Are small wings enough? How birds fly · What is a tailwind? A little pilot's guide.

Listen: two recordings below

The song

See a gold underline? Tap it. The little pilot has a note for you. The underlined words are buttons: each one opens a Little Blue Pilot Note.

Intro

(whistle hook) Hey! Hey! ! Hey!

Verse 1

tips a wing,
,
the Tailwind gang come whooshing in—
"Room for one more? Let's fly!"

Pre-Chorus

When the breeze is at your back,
you don't paddle, you don't push—

Chorus

Just go up, up, up! (up, up, up!)
,
up, up, up! (up, up, up!)
grab a buddy, take the ride!
Whoosh-a-whoosh, we glide (wheee!)
—
up, up, up, little pilot,
the sky is open wide!

Verse 2

and a giggle,
shows off,
we draw big hearts in
then we bonk 'em with a "bop!"

Pre-Chorus

Chorus

Bridge

Can you flap? (flap-flap!)
Can you glide? (wheee!)
Can you wave to a friend? (hi-i!)
Can you fly with me? (yeah!)

Outro

Up, up, up… and a-waaay!

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Little Blue Pilot Notes

Tail-wind

Wind that blows from behind you, pushing you along. With a tailwind you travel further and faster on the same effort, so a long trip takes less time and less work. Turn around and it becomes a headwind, shoving against your nose the whole way.

Pilots check which one they are getting before every single flight, because it changes everything about the trip.

Now look at who is arriving in this verse. The gang is called the Tailwind gang. These friends are the wind at your back.

Cruising Captain

Cruising means flying steady and easy. Not climbing, not diving, just going along comfortably, and Cruising Captain is the one who sets that pace.

The first thing this friend does is tip a wing, which is not decoration. Pilots really do rock their wings to say hello.

The song opens with a stranger arriving and immediately greeting you.

Wind Reader checks the sky

Somebody in the gang has to know what the air is doing. Wind Reader is the one who watches.

Because the sky talks. In clouds, in breezes, in the smell of rain. You just have to learn how to listen.

In track four, in the middle of a storm, Wind Reader gets the most important line in the song: feel the air.

let the happy wind decide

When the wind is already going your way, you do not paddle and you do not push. You let it carry you.

But look at the verb the song picked. Decide. Letting the wind choose where you end up is a small act of trust, which is harder than it sounds for anybody who likes being in charge.

Some days are like that. Not every good thing has to be fought for.

side by side by side

Flying wingtip to wingtip is real, and it has a name: formation. It takes enormous trust, because nobody in the group can hold their line unless everybody holds theirs.

Which is exactly why the line belongs in a song about friends. Trust is what makes formation possible and it is what makes friendship possible. The fact and the feeling are the same thing.

The sky is better with your friends in it.

Loop-the-loop

A full circle drawn in the air. Up, over, upside down for one thrilling second, and back around to where you started.

Here is why nobody falls out at the top: going round the circle presses you into your seat the whole way round. Upside down, you stay put. The circle holds you in.

It is exactly as fun as it sounds.

Aviation Ace

Aviation is the grown-up word for everything to do with flying, and an ace is somebody spectacularly good at it.

Every gang has one who cannot resist showing off. Here they are, looping the loop while everybody else is enjoying the ride.

the cotton clouds

The puffy pile-of-cotton-wool clouds. Their proper name is cumulus, which is Latin for heap.

Soft enough to draw big hearts in, which is what the gang does. Then they bonk the hearts with a bop.

Which is precisely how children say something lovely and then cover it up again.

Song details

From the manuscript: how the song is played, kept apart from the words.

Style, as the manuscript tags ithigh-energy kids' dance-pop, four-on-the-floor beat, whistle hook, group shouts, claps, 128 BPM

Tempo128 beats per minute

Arrangement notes

Bridge call & response

Listen

Two recordings of this song. Players load only when you press one, and nothing plays on its own.

Original recordings · August 2026Wings & Prayers

SpotifyPlay “Tailwind (Up, Up, Up)” on Spotify YouTubePlay the album recording on YouTube Apple MusicOpen “Tailwind (Up, Up, Up)” in Apple Music

As heard in the videos · September 2026Wings & Prayers: Second Flight

SpotifyPlay “Tailwind (Up, Up, Up) (Second Flight Version)” on Spotify YouTubePlay the music video Apple MusicOpen “Tailwind (Up, Up, Up) (Second Flight Version)” in Apple Music

Also: the Short on YouTube (opens in a new tab)

up, up, up, little pilot,
the sky is open wide!

A little pilot’s lesson

Joy is better together

Up, up, up… and a-waaay!

Also on the record: Tailwind (EDM Remix) (the album recording on YouTube, opens in a new tab), track 9 (tailwind, turned up loud).

Visit Tailwind Current in The Sky Map to find Tailwind (Up, Up, Up).

A WPAgency Studio story.